Silicon compounds derived from furfuryl alcohols and methods of preparation

Abstract

Novel silicon compounds containing a siloxane or silane moiety and at least one moiety derived from a furfuryl alcohol, and methods for their synthesis, are provided. The novel compounds may be used as surface modifying agents, surfactants, defoamers, and as monomers for silicone polymerization.

1 . A silicon compound or siloxane polymer comprising a siloxane or silane moiety and at least one furfuryl alcohol-derived moiety. 
     
     
         2 . The compound according to  claim 1 , further comprising an alkyl group bridging the siloxane or silane moiety and the furfuryl alcohol-derived moiety. 
     
     
         3 . The compound according to  claim 2 , wherein the alkyl group comprises about three carbon atoms. 
     
     
         4 . The compound according to  claim 1 , wherein the furfuryl alcohol is tetrahydrofurfuryl alcohol. 
     
     
         5 . The compound according to  claim 1 , wherein the silicon compound has formula (1): 
       
         
           
           
               
               
           
         
         wherein each X is independently a hydrogen, methyl, or hydroxyl group; n is an integer selected from 0 and 1; R 1  is C═O or C(O)NH, m is an integer from one to about six, when m is at least three, one of the internal CH 2  groups may be replaced with an oxygen atom, and R 2 , R 3 , and R 4  are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4  is an alkoxy or siloxy group. 
       
     
     
         6 . The compound according to  claim 5 , wherein m=3, n=0, and every X═H. 
     
     
         7 . The compound according to  claim 1 , having formula (2): 
       
         
           
           
               
               
           
         
         wherein n is an integer selected from 0 and 1; R 1  is C═O or C(O)NH, m is an integer from one to about six, and R 2 , R 3 , and R 4  are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4  is an alkoxy or siloxy group. 
       
     
     
         8 . The compound according to  claim 1 , wherein the silicon compound is tetrahydrofurfuryloxypropyltriethoxysilane. 
     
     
         9 . The compound according to  claim 1 , wherein the silicon compound is tetrahydrofurfuryloxypropylheptamethyltrisiloxane. 
     
     
         10 . The compound according to  claim 1 , wherein the silicon compound has formula (3): 
       
         
           
           
               
               
           
         
         wherein n is an integer selected from 0 and 1; R 1  is C═O or C(O)NH, m is an integer from 1 to about six, and R 2 , R 3 , and R 4  are independently a substituted or unsubstituted alkyl group having about one to about four carbon atoms, a substituted or unsubstituted alkoxy group having about one to about four carbon atoms, or a substituted or unsubstituted siloxy group, provided that at least one of R 2 , R 3 , and R 4  is an alkoxy or siloxy group. 
       
     
     
         11 . A surface modifying reagent comprising a silicon compound according to  claim 1 . 
     
     
         12 . A surfactant comprising a silicon compound according to  claim 1 . 
     
     
         13 . The compound according to  claim 1 , wherein the compound is a siloxane polymer containing a tetrahydrofurfuryloxyalkyl substitution. 
     
     
         14 . The compound according to  claim 1 , wherein the silicon compound is a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane copolymer. 
     
     
         15 . The compound according to  claim 1 , wherein the silicon compound is selected from the group consisting of a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylhydrogensiloxane terpolymer and a (tetrahydrofurfuryloxypropyl)methylsiloxane-dimethylsiloxane-methylvinylsiloxane terpolymer. 
     
     
         16 . An elastomeric and cross-linked product derived from at least one terpolymer according to  claim 15 . 
     
     
         17 . The compound according to  claim 1 , wherein the silicon compound is a siloxane homopolymer or copolymer having a hydride or vinyl terminal group. 
     
     
         18 . An elastomeric and cross-linked product derived from the copolymer or homopolymer according to  claim 17 . 
     
     
         19 . An elastomeric silane formed by the reaction of the polymer according to  claim 17  with a hydride- or vinyl-containing siloxane. 
     
     
         20 . A method for preparing a silicon compound comprising a siloxane or silane moiety and at least one furfuryl alcohol-derived moiety, the method comprising hydrosilylating a hydride functional silane or siloxane with at least one furfuryl alcohol containing a double bond to yield a hydrolytically stable silicon-to-carbon bond.